[4][5] In 1998, Eye Weekly (a Toronto Star newspaper-based division) hired Connolly to write columns on poetry, food, and theater, but by 2004, he left to start working as an editor for Coach House Press.
[2] In 1995, Connolly released his first collection of work, Asphalt cigar (Coach House Press), which was nominated for the League of Canadian Poets' Gerald Lampert Award for best first book of poetry.
[1] Upon releasing Asphalt cigar (1995), Connolly was one of six writers featured in Blues and True Concussions (House of Anansi Press, 1996), an anthology of new Toronto poets.
[6] In 2008, Connolly released his fourth collection of work, titled Revolver (House of Anansi Press), which was nominated for the 2009 Griffin Poetry Prize.
[11][12] During the 1990s, he published the early work of Canadians such as Lynn Crosbie, Gary Barwin, Daniel Jones, Stuart Ross and Gil Adamson in a collection titled Pink Dog Chapbook.